Lindsay Lohan: From Promising Actress to Box Office Babe to Jail

Lindsay Lohan -- where did it all go wrong? The 24-year-old actress has been sentenced to 90 days in jail and 90 days of rehab after a judge ruled that she violated her probation by missing alcohol education classes and failing to appear at a May DUI progress hearing.

We can pinpoint the exact moment when Britney Spears hit her lowest -- the great hair-shaving incident of 2007 and the follow-up umbrella attack. But with Lindsay, it's a little bit more difficult.

Looking back at her career, it seems like the signs that Lohan was spiraling out of control were far more subtle.

In 1998, Lohan made her big screen debut in the dual role of Hallie Parker and Annie James in 'The Parent Trap,' an update of the 1961 Hayley Mills vehicle. The cute redhead charmed audiences and held her own against veterans Natasha Richardson and Dennis Quaid. The movie earned her the Young Artist Award in 1999.

After 'Trap,' Lohan appeared in two made-for-TV movies on the Disney Channel -- 'Life Size' and 'Get a Clue' -- in 2000.

Meanwhile, she began dating Aaron Carter. The little brother of Backstreet Boy Nick, Aaron started a rift between Lindsay and fellow Disney tween star Hilary Duff, who also dated Carter around the same time. The feud between the two escalated and lasted for years before Duff finally declared "it's over."

She returned to the big screen in 2003 for 'Freaky Friday,' another remake of a Disney classic. The film was a big hit for the young actress, and she was named Breakthrough Female at the 2004 MTV Movie Awards.

However, it was 2004's 'Mean Girls' that propelled Lohan to true superstardom. The film was a box office hit, earning over $86 million made domestically, and proved that its star had stellar talent and impeccable comedic timing. Lohan again prevailed at the MTV Movie Awards in 2005, taking home the trophies for Best Female Performance and Best On-Screen Team with her co-stars.

While filming her next venture, 'Herbie: Fully Loaded,' Lohan recorded and released her first album, 'Speak.' The set went platinum in 2005.

The production of 'Herbie' -- released in theaters in 2005 -- was halted when Lohan experienced medical issues (she was hospitalized with a kidney infection) and was plagued by her personal drama (she'd recently broken up with boyfriend Wilmer Valderama). But the film was a moderate success, grossing $144 million worldwide.

It was during 'Herbie' that Lohan's off-screen antics truly began affecting her professional life. Stepping out with Nicole Richie in May 2005, the two caused a stir with their very thin frames. In place of her trademark 'Mean Girl' curves was a near-skeletal physique.

Lohan's family only added to her drama. Her relationship with Michael Lohan has long been contentious -- she even released a music video, titled 'Confessions of a Broken Heart,' chronicling their issues. More recently, Michael, who was arrested in 2005 for DUI, tried to force his daughter into rehab, something she tweeted furiously about. And although Lindsay and her father remain estranged, he appealed to judge Marsha Revel to keep his daughter from jail.

Meanwhile, her first big paycheck following her 'Mean Girls' success came in the 2006 film 'Just My Luck,' which received a 12 percent rating on Rotten Tomatoes and only made $17 million at the box office. Later that year, however, she starred in critical indie darlings 'A Prairie Home Companion' and 'Bobby.'

Lohan continued to struggle with her weight, and in 2006 appeared on the cover of Vanity Fair, purportedly admitted to bulimia. "I was sick. Everyone was scared. And I was scared too. I had people sit me down and say, 'You're going to die if you don't take care of yourself,'" she said in the interview.

However, the actress later claimed she was misquoted. But the year only continued to spiral for the starlet. During filming of the box office and critical bomb 'Georgia Rule,' she was hospitalized for exhaustion and received a scolding letter from producers.

"You and your representatives have told us that your various late arrivals and absences from the set have been the result of illness; today we were told it was 'heat exhaustion.' We are well aware that your ongoing all night heavy partying is the real reason for your so called 'exhaustion.' We refuse to accept bogus excuses for your behavior," the letter read.

The party continued for the rest of the year, with paparazzi following her every move. On November 27, 2006, photogs snapped her in Paris Hilton's car, alongside Spears, in Beverly Hills. Hilton and Lohan had just gotten over their feud, which was sparked by Lindsay's canoodling with Paris' ex, Stavros Niarchos.

Only a few days later, her rep admitted that Lohan was attending Alcoholics Anonymous meetings. But those clearly weren't enough, and in January 2007, she began her first stint in rehab. At the time, she was filming 'I Know Who Killed Me' and production had to be halted.

Later that year, in May, she entered rehab again. She would eventually seek treatment for a third time in early 2007, following two DUIs, the second of which was the catalyst for her 90-day jail sentence.

Although Lindsay has dated a string of men -- from Harry Morton to Jared Leto to Calum Best -- in 2008, she started dating Samantha Ronson. The two would fight, break up and get back together via their Twitter accounts. Michael Lohan went so far as to cite Ronson as the reason Lohan was having problems.

In a surprisingly candid interview with British paper The Sun, Lindsay revealed details of her relationship with Ronson as well as her drug use.

"I never really thought about women before, it kind of just happened with Samantha. It surprised me," Lindsay says. "If I wasn't with Samantha, I would probably be with a boy next. She's the only woman I've been attracted to. We love each other. We might reconcile the relationship, maybe. I don't know," she described.

"When my father was going public, that's when I hit rock bottom. I abused substances too much and it wasn't the answer to my problems. People need to know that," she recalled of her 2007 stints in rehab and troubles with her father.

It seems apparent that Lindsay's decline was gradual. What began with drama over a boy escalated into weight and possible eating disorder problems, and when combined with family troubles, the constant pressure of the paparazzi and her unhealthy relationship with Samantha Ronson, it's easy to see how Lindsay never really got her feet firmly back on the ground.

In our mind, the tipping point where her career took a backseat to her drama was 'I Know Who Killed Me.' The movie garnered an 8 percent rating on Rotten Tomatoes and grossed only $7.5 million at the box office. Appropriately enough, she played a dual role in this film, which brought her career full circle from 'The Parent Trap.' Yes, she's filmed things since then -- a stint on 'Ugly Betty,' from which she was allegedly fired, and 'Labor Pains,' which ended up going straight to TV -- but she hasn't been seen in a big screen hit in a long time.

She has a promising role in 'Machete' coming up, as well as the Linda Lovelace film 'Inferno,' which could also be her career savior. For her sake -- and ours -- we hope she can pull herself up and regain some of her former glory.

Lindsay Lohan sits with a message written on her fingernail before she is sentanced to 90 days jail by Judge Marsha Revel during her hearing at the Beverly Hills Courthouse on July 6, 2010. She sobbed and pleaded in court not to be thrown in jail, but troubled Hollywood starlet Lindsay Lohan had another, far less plaintive message for the judge, written on the fingernail of her middle finger.

I agree it is sad about her parents, but it's a little to late to do the right thing now! She's 24 years young, time for her to take control of her self, & what she want's, grow up..to @ least 24 & don't expect special treatment because she's a celeb., She did the crime, so be fair, she should do the time, just like anyone else.

Lindsay should be thanking the judge instead of her finger actions with the letters. Just goes to show she thinks she is above everyone else. She screws up before she goes to jail the judge needs to increase her time behind bars. The judge gave her the gift of her life and the phony tears act was pathetic.Lindsay's mother is all pissed off because now she may actually have to be a parent instead of trying to look and act like her daughters clone. Lindsay has no to blame but herself and she needs to grow up and accept the consequences.

I still remember when Dina Lohan was quoted in regards to Lindsey's partying at age 18 as "everybody does it." With an enabling parent, enabling friends, and enabling representatives, what hope is there for this girl than to get away from it all and have some time to really reflect on her life and where she is going. Perhaps jail will be the best thing for her.

Yep, the little tramp got what she deserves. But, like so many others have said, she's not even going to serve the full sentence, probably escape from rehab, and then be back out on the streets partying it up with all those other stupid f***s in Hollywood that just make a mockery of our court system. Here's what should of really happened, 90 days mandatory for the first DUI offense, add another 120 days mandatory for the second DUI offense, no time off for good behavior, then 90 days of rehab, which won't help a thing. On top of that, impose the max on the fines for both DUI offenses. The judge should have also found her in contempt of court for the little message on her finger nail and impose the max fine on that as well. As for her parents reaction and statements, get the f*** out! Both of them should realize that their daughter is a total loser! And yet, they expect that she should get preferential treatment? They're just as whacked as she is. Throw them in jail for 30 days just for their stupidity! But as with all Hollywood stories of this sort, it's just another slap on the wrist for the celebrity clan, but for the regular people like you and me, this would never happen in a million years. We get the book thrown at us, not once, but twice. Final thought, unbelieveable how the L.A. court system works!!!

I think everyone makes mistakes,I have seen people making much worse mistakes than this, like for example: killing someone,stealing or selling drugs. Just because she made the mistake of using drugs or Alcohol while driving doesn't mean that you need to put her in jail. I think you should help her by giving her another chance for her to Redeemed herself and show you that she can get help by going into rehab againg but this time; she would show you that she can get better by cleaning herself up and lead a good and healthy life eventually. I know she's a good Actress and a good singer, and besides she's smart, and she's a very beautiful young lady and I know she won't waste her life by using drugs or Alcohol she knows better than that. I hope you guys find it in your hearts to give her another chance.

Suck it up you rich spoiled little brat. If it were any other poverty stricken person they'd lock the door and throw away the jail!!! So so sick of these Hollywood brats being able to do what they want and get away with it and all with the support of their demented parents.

How gives a F .There is an other drunk that cries for sympathy instead of understanding that the damage to her self are FAR greater that the court can do.Yet this is the problem with addiction thy don't seem to understand they have a problem.As far as I'm concern they can drink or smoke them selves to death so far that are not endangering others.But they do.I think they are sick and need help the only problem is they have to ASK for

All she got is 90 days? She got off pretty easy, I'm sure if it were one of us, it would be alot more time involved. And as for her message on her fingernail.....just shows how mature and spoiled she really is. If I were the judge and knew that message was on there, she would have gotten as much time as I could give her. Hopefully no one in Hollywood will ever hire her for any other work after this.......

I think part of Lindsays downfall was hanging out with Paris Hilton, everyone one who has hung out with that twit including Brittney has hit bottom. The other part of Lindsay's downfall is her own mother or lack there of, useless Mother that is what Dina is, infact I would call her an absentee parent, because she could have stepped in long time ago. I only hope that Lindsay finally has a chance to clean up, before we read that she too has died of an overdose.

There have been so many young Hollywood types and children of celebrities who fall to the early partying, drinking and taking drugs. They have a target on their back by anyone who is more interested in their downfall (drug dealers). Its a tough life but I truly believe those starlets who went on to college survived better (Jodie Foster, Brooke Shields). With an education you don't need someone else to define you. I think Myley Cyrus will be the next to fall hard. Wise up Hollywood use that money to educate your kids.